HUT77388A - Ciklopeptolidok és gyógyszerkészítményekben való felhasználásuk - Google Patents

Ciklopeptolidok és gyógyszerkészítményekben való felhasználásuk Download PDF

Info

Publication number: HUT77388A
Authority: HU; Hungary
Prior art keywords: formula; compounds; leu; hydrogen; alkyl
Prior art date: 1994-07-27

Application number

HU9700226A

Other languages

English (en)

Hungarian (hu)

Inventor

Michael Morris Dreyfuss

Carolyn Ann Foster

Hans-Ulrich Naegeli

Berndt Oberhauser

Original Assignee

Novartis Ag.

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1994-07-27

Filing date

1995-07-26

Publication date

1998-04-28

1994-07-27 Priority claimed from GB9415168A external-priority patent/GB9415168D0/en

1995-03-03 Priority claimed from GBGB9504332.9A external-priority patent/GB9504332D0/en

1995-07-26 Application filed by Novartis Ag. filed Critical Novartis Ag.

1998-04-28 Publication of HUT77388A publication Critical patent/HUT77388A/hu

Links

239000008194 pharmaceutical composition Substances 0.000 title claims description 7
238000011282 treatment Methods 0.000 claims abstract description 10
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 8
201000010099 disease Diseases 0.000 claims abstract description 7
150000001875 compounds Chemical class 0.000 claims description 221
239000001257 hydrogen Substances 0.000 claims description 56
229910052739 hydrogen Inorganic materials 0.000 claims description 56
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 48
125000000217 alkyl group Chemical group 0.000 claims description 44
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 42
206010029897 Obsessive thoughts Diseases 0.000 claims description 36
238000002360 preparation method Methods 0.000 claims description 34
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 31
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 30
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 27
-1 cyano, thiocarbamoyl Chemical group 0.000 claims description 27
239000000203 mixture Substances 0.000 claims description 27
125000004093 cyano group Chemical group *C#N 0.000 claims description 18
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
229910052736 halogen Inorganic materials 0.000 claims description 16
150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 15
108090000765 processed proteins & peptides Proteins 0.000 claims description 14
239000002253 acid Substances 0.000 claims description 13
125000003545 alkoxy group Chemical group 0.000 claims description 13
VDCLCAXYTCLVQY-CTVGSUQISA-N 2-[(3s,6s,9s,15s,18s,21s,24s,27s)-15,18-di(butan-2-yl)-6-[(4-methoxyphenyl)methyl]-3,10,16,19,22,28-hexamethyl-2,5,8,11,14,17,20,23,26,29-decaoxo-9,24,27-tri(propan-2-yl)-1,4,7,10,13,16,19,22,25,28-decazabicyclo[28.4.0]tetratriacontan-21-yl]acetic acid Chemical compound C([C@H]1C(=O)N[C@@H](C)C(=O)N2CCCCC2C(=O)N(C)[C@@H](C(C)C)C(=O)N[C@H](C(=O)N(C)[C@@H](CC(O)=O)C(=O)N(C)[C@@H](C(C)CC)C(=O)N(C)[C@H](C(NCC(=O)N(C)[C@@H](C(C)C)C(=O)N1)=O)C(C)CC)C(C)C)C1=CC=C(OC)C=C1 VDCLCAXYTCLVQY-CTVGSUQISA-N 0.000 claims description 12
150000002367 halogens Chemical class 0.000 claims description 12
238000000034 method Methods 0.000 claims description 11
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 9
CZCIKBSVHDNIDH-NSHDSACASA-N N(alpha)-methyl-L-tryptophan Chemical group C1=CC=C2C(C[C@H]([NH2+]C)C([O-])=O)=CNC2=C1 CZCIKBSVHDNIDH-NSHDSACASA-N 0.000 claims description 8
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 8
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 8
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 8
230000002538 fungal effect Effects 0.000 claims description 8
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 8
125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
125000003831 tetrazolyl group Chemical group 0.000 claims description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
239000003814 drug Substances 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 7
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 6
QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 claims description 6
QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 claims description 6
239000001963 growth medium Substances 0.000 claims description 6
125000005842 heteroatom Chemical group 0.000 claims description 6
239000003960 organic solvent Substances 0.000 claims description 6
230000008569 process Effects 0.000 claims description 6
229920002554 vinyl polymer Polymers 0.000 claims description 6
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
239000003153 chemical reaction reagent Substances 0.000 claims description 5
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
230000002401 inhibitory effect Effects 0.000 claims description 5
125000005473 octanoic acid group Chemical class 0.000 claims description 5
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 4
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical class CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 4
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 claims description 4
150000001412 amines Chemical class 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 4
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 4
MCQRPQCQMGVWIQ-UHFFFAOYSA-N boron;methylsulfanylmethane Chemical compound [B].CSC MCQRPQCQMGVWIQ-UHFFFAOYSA-N 0.000 claims description 4
239000003054 catalyst Substances 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
150000002148 esters Chemical class 0.000 claims description 4
PTXVSDKCUJCCLC-UHFFFAOYSA-N 1-hydroxyindole Chemical compound C1=CC=C2N(O)C=CC2=C1 PTXVSDKCUJCCLC-UHFFFAOYSA-N 0.000 claims description 3
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 3
230000002378 acidificating effect Effects 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
230000009467 reduction Effects 0.000 claims description 3
125000003107 substituted aryl group Chemical group 0.000 claims description 3
AFENDNXGAFYKQO-UHFFFAOYSA-N 2-hydroxybutyric acid Chemical group CCC(O)C(O)=O AFENDNXGAFYKQO-UHFFFAOYSA-N 0.000 claims description 2
GDFAOVXKHJXLEI-VKHMYHEASA-N N-methyl-L-alanine Chemical compound C[NH2+][C@@H](C)C([O-])=O GDFAOVXKHJXLEI-VKHMYHEASA-N 0.000 claims description 2
AKCRVYNORCOYQT-YFKPBYRVSA-N N-methyl-L-valine Chemical group CN[C@@H](C(C)C)C(O)=O AKCRVYNORCOYQT-YFKPBYRVSA-N 0.000 claims description 2
239000000443 aerosol Substances 0.000 claims description 2
230000001476 alcoholic effect Effects 0.000 claims description 2
239000003513 alkali Substances 0.000 claims description 2
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 2
239000002585 base Substances 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
125000001246 bromo group Chemical group Br* 0.000 claims description 2
235000014121 butter Nutrition 0.000 claims description 2
239000006071 cream Substances 0.000 claims description 2
CLUOCCWZZAGLPM-UHFFFAOYSA-N diphenyl-sulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound C=1C=CC=CC=1P(=S)(S)C1=CC=CC=C1 CLUOCCWZZAGLPM-UHFFFAOYSA-N 0.000 claims description 2
125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
230000002140 halogenating effect Effects 0.000 claims description 2
229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
229910052744 lithium Inorganic materials 0.000 claims description 2
239000006210 lotion Substances 0.000 claims description 2
229910052987 metal hydride Inorganic materials 0.000 claims description 2
150000004681 metal hydrides Chemical class 0.000 claims description 2
239000011707 mineral Substances 0.000 claims description 2
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
239000012038 nucleophile Substances 0.000 claims description 2
150000002902 organometallic compounds Chemical class 0.000 claims description 2
230000003647 oxidation Effects 0.000 claims description 2
238000007254 oxidation reaction Methods 0.000 claims description 2
150000003839 salts Chemical class 0.000 claims description 2
238000010561 standard procedure Methods 0.000 claims description 2
150000003463 sulfur Chemical class 0.000 claims description 2
230000001225 therapeutic effect Effects 0.000 claims description 2
238000011200 topical administration Methods 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims 4
WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims 2
125000001424 substituent group Chemical group 0.000 claims 2
125000000547 substituted alkyl group Chemical group 0.000 claims 2
230000029936 alkylation Effects 0.000 claims 1
238000005804 alkylation reaction Methods 0.000 claims 1
OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims 1
238000006555 catalytic reaction Methods 0.000 claims 1
229910052801 chlorine Inorganic materials 0.000 claims 1
125000001309 chloro group Chemical group Cl* 0.000 claims 1
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims 1
238000009472 formulation Methods 0.000 claims 1
239000002516 radical scavenger Substances 0.000 claims 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
229910052721 tungsten Inorganic materials 0.000 claims 1
239000010937 tungsten Substances 0.000 claims 1
239000003112 inhibitor Substances 0.000 abstract description 4
230000002757 inflammatory effect Effects 0.000 abstract description 2
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 342
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 166
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 166
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 153
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 108
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 84
XJODGRWDFZVTKW-LURJTMIESA-N (2s)-4-methyl-2-(methylamino)pentanoic acid Chemical group CN[C@H](C(O)=O)CC(C)C XJODGRWDFZVTKW-LURJTMIESA-N 0.000 description 66
239000000243 solution Substances 0.000 description 56
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 48
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
210000004027 cell Anatomy 0.000 description 44
239000000741 silica gel Substances 0.000 description 44
229910002027 silica gel Inorganic materials 0.000 description 44
239000002904 solvent Substances 0.000 description 39
BKBMACKZOSMMGT-UHFFFAOYSA-N methanol;toluene Chemical compound OC.CC1=CC=CC=C1 BKBMACKZOSMMGT-UHFFFAOYSA-N 0.000 description 38
230000002829 reductive effect Effects 0.000 description 34
SJZRECIVHVDYJC-UHFFFAOYSA-N 4-hydroxybutyric acid Chemical compound OCCCC(O)=O SJZRECIVHVDYJC-UHFFFAOYSA-N 0.000 description 32
238000004809 thin layer chromatography Methods 0.000 description 31
238000010828 elution Methods 0.000 description 26
108010064593 Intercellular Adhesion Molecule-1 Proteins 0.000 description 25
102000015271 Intercellular Adhesion Molecule-1 Human genes 0.000 description 25
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 22
239000011541 reaction mixture Substances 0.000 description 22
239000012043 crude product Substances 0.000 description 18
239000006260 foam Substances 0.000 description 17
239000002609 medium Substances 0.000 description 17
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
108010000134 Vascular Cell Adhesion Molecule-1 Proteins 0.000 description 15
102100023543 Vascular cell adhesion protein 1 Human genes 0.000 description 15
LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 15
239000002953 phosphate buffered saline Substances 0.000 description 15
239000012071 phase Substances 0.000 description 14
239000000047 product Substances 0.000 description 13
DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 13
OXEUETBFKVCRNP-UHFFFAOYSA-N 9-ethyl-3-carbazolamine Chemical compound NC1=CC=C2N(CC)C3=CC=CC=C3C2=C1 OXEUETBFKVCRNP-UHFFFAOYSA-N 0.000 description 12
108010024212 E-Selectin Proteins 0.000 description 12
102100023471 E-selectin Human genes 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
238000003556 assay Methods 0.000 description 12
229910052938 sodium sulfate Inorganic materials 0.000 description 12
235000011152 sodium sulphate Nutrition 0.000 description 12
229940126062 Compound A Drugs 0.000 description 11
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 11
239000012044 organic layer Substances 0.000 description 11
229910000030 sodium bicarbonate Inorganic materials 0.000 description 11
235000017557 sodium bicarbonate Nutrition 0.000 description 11
238000012360 testing method Methods 0.000 description 11
238000004448 titration Methods 0.000 description 11
239000010410 layer Substances 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
230000002441 reversible effect Effects 0.000 description 9
229920006395 saturated elastomer Polymers 0.000 description 9
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
238000004587 chromatography analysis Methods 0.000 description 8
230000005764 inhibitory process Effects 0.000 description 8
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 8
238000010898 silica gel chromatography Methods 0.000 description 8
108091003079 Bovine Serum Albumin Proteins 0.000 description 7
239000012894 fetal calf serum Substances 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
210000002889 endothelial cell Anatomy 0.000 description 6
DAEPDZWVDSPTHF-UHFFFAOYSA-M sodium pyruvate Chemical compound [Na+].CC(=O)C([O-])=O DAEPDZWVDSPTHF-UHFFFAOYSA-M 0.000 description 6
239000008259 solid foam Substances 0.000 description 6
UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 6
229920001817 Agar Polymers 0.000 description 5
238000002835 absorbance Methods 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
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230000037396 body weight Effects 0.000 description 5
210000002510 keratinocyte Anatomy 0.000 description 5
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
239000007787 solid Substances 0.000 description 5
238000010186 staining Methods 0.000 description 5
239000000126 substance Substances 0.000 description 5
HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 4
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
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230000004071 biological effect Effects 0.000 description 4
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230000003013 cytotoxicity Effects 0.000 description 4
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239000008367 deionised water Substances 0.000 description 4
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239000000843 powder Substances 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
239000012138 yeast extract Substances 0.000 description 4
238000005160 1H NMR spectroscopy Methods 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
241000283707 Capra Species 0.000 description 3
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108090000695 Cytokines Proteins 0.000 description 3
206010028980 Neoplasm Diseases 0.000 description 3
229930182555 Penicillin Natural products 0.000 description 3
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 3
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239000007864 aqueous solution Substances 0.000 description 3
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125000004432 carbon atom Chemical group C* 0.000 description 3
230000006727 cell loss Effects 0.000 description 3
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238000000855 fermentation Methods 0.000 description 3
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ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 3
238000002329 infrared spectrum Methods 0.000 description 3
238000002955 isolation Methods 0.000 description 3
210000000265 leukocyte Anatomy 0.000 description 3
XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 3
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DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
210000003606 umbilical vein Anatomy 0.000 description 1
230000002792 vascular Effects 0.000 description 1
230000003612 virological effect Effects 0.000 description 1
239000003643 water by type Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N1/00—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
- C12N1/14—Fungi; Culture media therefor
- C12N1/145—Fungal isolates
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K11/00—Depsipeptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K11/02—Depsipeptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof cyclic, e.g. valinomycins ; Derivatives thereof
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12R—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
- C12R2001/00—Microorganisms ; Processes using microorganisms
- C12R2001/645—Fungi ; Processes using fungi

Landscapes

Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Medicinal Chemistry (AREA)
General Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Genetics & Genomics (AREA)
Immunology (AREA)
Zoology (AREA)
Virology (AREA)
Biochemistry (AREA)
Wood Science & Technology (AREA)
Biotechnology (AREA)
Biomedical Technology (AREA)
Tropical Medicine & Parasitology (AREA)
Molecular Biology (AREA)
Botany (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Biophysics (AREA)
General Engineering & Computer Science (AREA)
Communicable Diseases (AREA)
Rheumatology (AREA)
Dermatology (AREA)
Oncology (AREA)
Microbiology (AREA)
Pulmonology (AREA)
Mycology (AREA)
Hematology (AREA)
Transplantation (AREA)
Diabetes (AREA)
Orthopedic Medicine & Surgery (AREA)

HU9700226A 1994-07-27 1995-07-26 Ciklopeptolidok és gyógyszerkészítményekben való felhasználásuk HUT77388A (hu)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB9415168A GB9415168D0 (en)	1994-07-27	1994-07-27	Organic compounds
GBGB9504332.9A GB9504332D0 (en)	1995-03-03	1995-03-03	Organic compounds

Publications (1)

Publication Number	Publication Date
HUT77388A true HUT77388A (hu)	1998-04-28

Family

ID=26305345

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HU9700226A HUT77388A (hu)	1994-07-27	1995-07-26	Ciklopeptolidok és gyógyszerkészítményekben való felhasználásuk

Country Status (26)

Country	Link
US (1)	US6013627A (es)
EP (1)	EP0775158B1 (es)
JP (1)	JP3425763B2 (es)
KR (1)	KR100378974B1 (es)
CN (1)	CN1116304C (es)
AT (1)	ATE187461T1 (es)
AU (1)	AU702332B2 (es)
BR (1)	BR9508342A (es)
CA (1)	CA2192786C (es)
CY (1)	CY2225B1 (es)
CZ (1)	CZ289311B6 (es)
DE (1)	DE69513837T2 (es)
DK (1)	DK0775158T3 (es)
ES (1)	ES2142490T3 (es)
FI (1)	FI970279A0 (es)
GR (1)	GR3032698T3 (es)
HK (1)	HK1014011A1 (es)
HU (1)	HUT77388A (es)
MX (1)	MX9606494A (es)
NO (1)	NO970340D0 (es)
NZ (1)	NZ291168A (es)
PL (1)	PL181990B1 (es)
PT (1)	PT775158E (es)
RU (1)	RU2155772C2 (es)
SK (1)	SK11797A3 (es)
WO (1)	WO1996003430A1 (es)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6187757B1 (en) *	1995-06-07	2001-02-13	Ariad Pharmaceuticals, Inc.	Regulation of biological events using novel compounds
US6011136A (en) *	1995-11-21	2000-01-04	Novartis Ag	Cyclopeptolides
WO1999014082A1 (en)	1996-09-18	1999-03-25	Minnesota Mining And Manufacturing Company	Adhesively-bonded inflatable restraint and method of making
US6365619B1 (en)	1999-07-22	2002-04-02	Novartis Ag	Treatment of arteriosclerosis
ES2219388T3 (es) *	1999-08-24	2004-12-01	Ariad Gene Therapeutics, Inc.	28-epi-rapalogos.
US7067526B1 (en)	1999-08-24	2006-06-27	Ariad Gene Therapeutics, Inc.	28-epirapalogs
WO2002034283A2 (en) *	2000-10-27	2002-05-02	Novartis Ag	Vegh inhibitors and their use
GB0028367D0 (en) *	2000-11-21	2001-01-03	Celltech Chiroscience Ltd	Chemical compounds
GB0101598D0 (en) *	2001-01-22	2001-03-07	Novartis Ag	Organic compounds
DE60331367D1 (de)	2002-12-30	2010-04-01	Angiotech Int Ag	Wirkstofffreisetzung von schnell gelierender polymerzusammensetzung
CA2711765A1 (en)	2008-01-11	2009-07-16	Massachusetts Eye & Ear Infirmary	Conditional-stop dimerizable caspase transgenic animals
CA2905229C (en)	2013-06-11	2023-10-10	Clontech Laboratories, Inc.	Protein enriched microvesicles and methods of making and using the same

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4443367A (en) *	1982-04-08	1984-04-17	Monsanto Company	Peptide and peptolide substrates for mammalian collagenase
US4425428A (en) *	1982-04-08	1984-01-10	Monsanto Company	Novel peptide and peptolide substrates for mammalian collagenase
DE3851268T2 (de) *	1987-06-19	1995-01-26	Sandoz Ag	Zyklische Peptolide.
DE3832059A1 (de) *	1988-09-21	1990-03-29	Howaldtswerke Deutsche Werft	Tauchtiefengesteuerte ausblasventil-einrichtung
DE3832362A1 (de) *	1988-09-23	1990-03-29	Sandoz Ag	Neue cyclopeptolide, verfahren zu ihrer herstellung und ihre verwendung

1995
- 1995-07-26 ES ES95928473T patent/ES2142490T3/es not_active Expired - Lifetime
- 1995-07-26 MX MX9606494A patent/MX9606494A/es not_active IP Right Cessation
- 1995-07-26 PT PT95928473T patent/PT775158E/pt unknown
- 1995-07-26 US US08/776,440 patent/US6013627A/en not_active Expired - Fee Related
- 1995-07-26 BR BR9508342A patent/BR9508342A/pt not_active Application Discontinuation
- 1995-07-26 HU HU9700226A patent/HUT77388A/hu unknown
- 1995-07-26 PL PL95317349A patent/PL181990B1/pl unknown
- 1995-07-26 CN CN95194370A patent/CN1116304C/zh not_active Expired - Fee Related
- 1995-07-26 NZ NZ291168A patent/NZ291168A/en unknown
- 1995-07-26 RU RU97102700/04A patent/RU2155772C2/ru not_active IP Right Cessation
- 1995-07-26 DE DE69513837T patent/DE69513837T2/de not_active Expired - Fee Related
- 1995-07-26 CA CA002192786A patent/CA2192786C/en not_active Expired - Fee Related
- 1995-07-26 EP EP95928473A patent/EP0775158B1/en not_active Expired - Lifetime
- 1995-07-26 JP JP50548596A patent/JP3425763B2/ja not_active Expired - Fee Related
- 1995-07-26 AU AU32221/95A patent/AU702332B2/en not_active Ceased
- 1995-07-26 SK SK117-97A patent/SK11797A3/sk unknown
- 1995-07-26 CZ CZ1997221A patent/CZ289311B6/cs not_active IP Right Cessation
- 1995-07-26 AT AT95928473T patent/ATE187461T1/de not_active IP Right Cessation
- 1995-07-26 WO PCT/EP1995/002966 patent/WO1996003430A1/en active IP Right Grant
- 1995-07-26 DK DK95928473T patent/DK0775158T3/da active
- 1995-07-26 KR KR1019970700504A patent/KR100378974B1/ko not_active IP Right Cessation
1997
- 1997-01-23 FI FI970279A patent/FI970279A0/fi unknown
- 1997-01-27 NO NO970340A patent/NO970340D0/no unknown
1998
- 1998-12-23 HK HK98115157A patent/HK1014011A1/xx unknown
2000
- 2000-02-18 GR GR20000400396T patent/GR3032698T3/el unknown
2001
- 2001-06-08 CY CY0100011A patent/CY2225B1/xx unknown

Also Published As

Publication number	Publication date
NZ291168A (en)	1998-06-26
FI970279A (fi)	1997-01-23
AU702332B2 (en)	1999-02-18
US6013627A (en)	2000-01-11
DE69513837D1 (de)	2000-01-13
RU2155772C2 (ru)	2000-09-10
NO970340L (no)	1997-01-27
ES2142490T3 (es)	2000-04-16
GR3032698T3 (en)	2000-06-30
EP0775158B1 (en)	1999-12-08
PL181990B1 (pl)	2001-10-31
HK1014011A1 (en)	1999-09-17
KR100378974B1 (ko)	2003-10-08
JP3425763B2 (ja)	2003-07-14
NO970340D0 (no)	1997-01-27
DK0775158T3 (da)	2000-05-22
CN1154705A (zh)	1997-07-16
PT775158E (pt)	2000-05-31
BR9508342A (pt)	1997-10-21
WO1996003430A1 (en)	1996-02-08
JPH10504540A (ja)	1998-05-06
ATE187461T1 (de)	1999-12-15
CA2192786A1 (en)	1996-02-08
CN1116304C (zh)	2003-07-30
CY2225B1 (en)	2003-04-18
FI970279A0 (fi)	1997-01-23
CZ22197A3 (en)	1997-05-14
PL317349A1 (en)	1997-04-01
SK11797A3 (en)	1997-07-09
AU3222195A (en)	1996-02-22
CA2192786C (en)	2009-06-16
DE69513837T2 (de)	2000-05-18
MX9606494A (es)	1997-03-29
CZ289311B6 (cs)	2001-12-12
EP0775158A1 (en)	1997-05-28

Publication	Publication Date	Title
US5767069A (en)	1998-06-16	Cyclosporins
HUT77388A (hu)	1998-04-28	Ciklopeptolidok és gyógyszerkészítményekben való felhasználásuk
KR101566046B1 (ko)	2015-11-04	환형 화합물을 생산하는 미생물
DE68921128T2 (de)	1995-09-14	Pipocolinsäure enthaltende cyclische Peptolide, ihre Herstellung und sie enthaltende Zusammensetzungen.
KR920006881B1 (ko)	1992-08-21	프리파스타틴(plipastatin)의 제조방법
JP2003529585A (ja)	2003-10-07	ケモカインレセプターアンタゴニスト
AU712900B2 (en)	1999-11-18	Cyclopeptolides
US6251885B1 (en)	2001-06-26	Cytotrienins, process for preparing the same and anti-tumor agent
US7803600B2 (en)	2010-09-28	Micromonospora species that produces a bafilomycin-like metabolite
US7112581B2 (en)	2006-09-26	Macrocyclic lactams
JPH08301862A (ja)	1996-11-19	Ｐｅｎｉｃｉｌｌｉｕｍ種の抗生物質シリアノンおよびその化学誘導体並びにその製造法および使用